


Curiosity Doesn't Necessary Kill

by FarTheSuperFan



Category: Supernatural
Genre: Anal Fingering, Anal Fisting, M/M, Masturbation, Voyeurism
Language: English
Status: Completed
Published: 2014-09-21
Updated: 2014-09-21
Packaged: 2018-02-18 07:57:12
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,800
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2340911
Author URL: https://archiveofourown.org/users/FarTheSuperFan/pseuds/FarTheSuperFan
Summary: <blockquote class="userstuff">
              <p>Sam Winchester is a curious kid, and Dean Winchester is very promiscuous.</p>
            </blockquote>





	Curiosity Doesn't Necessary Kill

**Author's Note:**

> Sam is underage, around fourteen.

Sam Winchester was a curious kid. Always had been and, considering the way he’d been raised, he had every right to be. It would sometimes get on Dean’s nerves, though; occasionally he’d feel as if Sam was interrogating him, or just trying to annoy the holy hell out of him with the constant observations and questioning. “How come we don’t have a mom,” “Why do we always have to move around,” “Where’d dad go?” It took some getting used to, but Dean eventually figured out the best ways to answer these types of questions: usually with a witty retort, or some kind of partial-truth answer. He never told Sam the whole truth about who they are and what their Dad does, though. He wanted Sam to be a kid just a little while longer, wanted to protect him and keep him safe. When Sam started asking questions about how to talk to girls, well, Dean was always comfortable with those sorts of questions. Hell, he was comfortable rattling off about at least a dozen answers to every sex and romance question Sam had asked him. Dean was comfortable answers every sex question, except one.

“You want to know how to do what?” Dean asked.

“How to make…you know…masturbating…more satisfying,” Sam replied.

Dean stood there, in the middle of this week’s grimy motel room, eyeing his little brother. Of course Dean knew how to make masturbating more satisfying. He picked up little tips and tricks along the way while hooking up with various women of all ages and sexual experiences. This one Texan bar tender that had served their dad at some local diner opened him up, quite literally, to the stimulation of his prostate. It was weird at first, and caught him completely off-guard, but he was too immersed in the pleasure it brought him to stop and question the twenty-something waitress. It was the most satisfying sex he’d ever had, and he continued that practice by himself almost daily. But telling Sam all of this…well, Sam might be disgusted by Dean, and Dean just couldn’t live with himself if his brother thought he was a freak and refused to even look at him. That was the worse case scenario, of course.

“What? They don’t teach this in sex ed, Sammy?” Dean replied sarcastically, with a look that, very poorly, tried to cover up his discomfort.

“Dean, I’m serious.” Little Sammy, always so serious.

Dean hesitated for a little bit, shifting his weight between his feet. He looked briefly around the room, seeming a little too interested in the patterns of the uselessly thin curtains and the odd stains that littered the grey couch. After a few moments, he sighed and rolled his eyes, closing them before meeting Sam’s.

“Okay, listen. There is this one thing that I do sometimes. But you can’t freak out. I swear if you freak out, I’m –”

“Dee, just tell me,” Sam interrupted, annoyed. He knew his brother had a reputation of being promiscuous. In fact, Dean practically made sure Sam knew the details of each one-night stand, to the point where Sam felt as if he had watched the scenes Dean described, instead of feeling like he was listening to a story. While he waited for Dean to speak again, Sam’s eyes never left Dean’s face.

“Don’t ask me how I know, but…play with your ass occasionally, you know, like when you’re rubbing one off in the shower or something.” Dean’s answer was not at all what Sam expected. Sam wasn’t really sure just what he was expecting, but that certainly was not it. As embarrassed and uncomfortable as Dean was, he studied Sam’s face, looking for any signs of disgust or rejection. Instead, he saw Sam’s brows furrow together, a quizzical expression crossing his still delicate teenage features.

“Play with my ass? How?”

“Jesus, Sammy, you can google that! You don’t need me to break it down for you.” Dean turned away, embarrassed. But he knew from previous experience that Sam was going to keep prying unless he got a direct answer.

“I can show you, if you want,” muttered Dean, barely opening his mouth to speak the words. “If you’re really interested, I can show you what I do.” He couldn’t resist those puppy dog eyes Sam threw at him. 

Sam was breathless as Dean began stripping off his shirt and shedding his pants. Sure, he’s seen his older brother naked before, close quarters and all was part of the lifestyle, but this felt different. All of these new feelings Sam was experiencing went straight to his quickly hardening dick. He proceeded to watch closely, forcing himself to breathe as Dean slowly, almost teasingly, removed his boxers. With his clothes now in a pile on the floor in front of Sam, Dean turned and walked slowly to the bed, trying not to smile as he felt Sam’s eyes on his ass, and lied down on his back.

When he finally remembered that, yes, he did have full control over his body, Sam cautiously followed Dean into bed, sitting on his knees in front of Dean’s spread legs. Dean wasn’t much for exhibitionism, but he laughed under his breath when he saw Sam seated in front of him. He mumbled something, and then closed his eyes, slowly getting himself in the mood. It was in this moment that Dean figured out he definitely has stage fright.

Dean circled his nipple with the pad of one of his fingers, slowly and gently at first, then began to pinch it. Small moans managed to escape from his mouth as he bit his bottom lip to quiet himself, and couldn’t stop himself from rolling his hips. Sam shuddered and almost couldn’t resist grabbing his hard-on through his jeans. He knew that his was a big step for Dean, and he didn’t want to distract him; he wanted Dean to stay in the moment as if his little brother wasn’t even there. Both nipples were red and hard now, and Dean continued to move down his body, ghosting over the area right above where his treasure trail was the thickest. Dean was really sensitive there, on his lower belly, and it tickled just barely running his fingers over it. He grinned subtly and took his dick in his hand, flicking his wrist to the very top of his penis, lathering the rest of his member in pre-cum. A high-pitch moan came out of Sam, who froze as soon as the sound left his mouth. Dean’s eyes fluttered, but he refused to open them and acknowledge Sam.

He worked his dick faster now, slicking his fingers in enough pre-cum to provide lubrication. The hand that was previously stroking his dick moved down to his ass, being replaced by his other hand. Dean treated his ass like he did his nipples, circling his tight entrance and occasionally dipping a finger in, moaning. Sam blushed and palmed the hard member in his jeans, never taking his eyes off of his older brother. After quite some time, Dean began fucking himself on one finger, excess lube causing the most obscene and delicious noises imaginable. Squeezing his eyes tighter, Dean inserted another finger, thrusting them in and out ferociously, moaning like a whore. Dean’s been fingering himself for a while now, ever since that waitress back in Texas. By now, he’s figured out what he likes, what he doesn’t, and how to nail his prostate to create the most blinding orgasms without even laying a hand on his penis. Once, while Sam was at school and John was away on a hunt, he spent the entire day fingering himself. He especially loved fucking himself without lube, loved the wonderful pleasurable burn it created. Dean also figured out that the necks of empty beer bottles provided even more pleasure than his own fingers. They could go deeper than his own fingers ever could, and could stretch him wider. 

“Oh, god,” Dean moaned, rolling his lips and scissoring his fingers. He had abandoned his dick by now, not purposefully though. He was just too caught up in the sensation of rubbing against his prostate to focus on his dick. Besides, playing with his ass provided much more pleasure than stroking his dick. Three fingers in now, and he already felt so full. Wanting to provide a show for Sam, he attempted four. Dean had never done any more than three, so he used his free hand to grab the lube from under his pillow and squirt it on his fingers generously, still avoiding Sam’s face. 

“Oh, fuck. God dammit, oh my god, ahhhh,” Dean yelled, shoving a fourth finger in his ass to accompany the previous three. “Yes, yes…fuck, yes!” Dean’s face contorted and he bit his lip. He wasn’t really sure when he put his fifth finger in, but he felt the extra burn and fisted himself faster. “Shit, oh my god. Fuck! Yes!” 

Sam was transfixed by the sight of Dean’s entire fist in his own ass, and it was just too much for him to handle. Without even thinking, Sam yanked his zipper down and grabbed for his cock underneath the elastic of his boxers. Shuddering when his hand wrapped around his dick, Sam practically screamed a chant of “god fucking dammit, oh my god, Dean, Dean, yes! Dean!” Coming with Dean’s name on his lips, he looked up at his older brother, who was looking right back at him intently. Dean’s face was red, and his hair stuck to his forehead. He looked fucking wrecked. Dean continued to fuck himself with his fist while looking at Sam, without even blinking. He came with a scream, continuing to shove his fist in and out until the last drop of come landed on his chest. 

Breathlessly, Dean watched Sam come down from his own high, all red-faced and sweaty, just like his older brother. Sam crawled up next to Dean, leaving his previous position from in between Dean’s legs. For a minute, both of them were quiet, trying to control their breathing.

“Holy shit,” Dean finally breathed, breaking the silence.

“I know,” Sam agreed. “Thanks, for showing me that, Dee,” he said, contouring himself against Dean’s solid, strong figure. Dean brushed the hair out of his baby brother’s face. 

“You’re welcome, Sammy. But don’t go using up all the hot water in the shower now that you know this. I need my own alone time, too, you know.”

Sam shot him a look. Not quite a bitch face, like Dean expected. There was something hopeful in his eyes, something clouded with lust. Something that said Sam wanted this to continue, to go further. Dean was screwed. “Jerk,” Sam grinned, nudging his brother lightly.

“Bitch,” Dean smiled.

**Author's Note:**

> This is my first time writing fanfic. Comments appreciated!


End file.
